The History of Guybrush Threepwood
by Archived-AndInactive
Summary: This story attempts to explore a bit of Guybrush's childhood, and provide an explanation for some of the biggest mysteries surrounding our bumbling pirate hero. What was it that made Guybrush so... Guybrush-y?
1. Chapter 1

**Hello everyone! So, this is my first ever fanfiction on this site, though I've written a few things before, and I'm excited! This story was inspired by the recent release of the new sequel Tales of Monkey Island and the re-release of both Secret of Monkey Island and the upcoming LeChuck's Revenge.**

**This story was designed to basically explore just a snippet of Guybrush's past and hopefully answer some questions about how he became so... Guybrush-y. I suppose it's a bit predictable at times, and it's not really the best thing I've ever written, but I think it's a pretty good story nonetheless. Enoy!**

**Every time you read and don't review, LeChuck kills an innocent pirate. So please R&R for me!**

Ruth turned her face upwards a little bit to better catch the light breeze that was gracing Pillage Island that afternoon. She was leaning against the railing of their island's only dock, enjoying the pleasant weather. She slowly pulled the gold locket she was wearing off and turned it over in her fingers.

"Hey mom?"

Ruth nearly jumped out of her skin at the casual greeting. "Huh? Don't sneak up on me like that, Myra!"

"Sorry. What's that you're looking at?" Myra gestured to the golden necklace sparkling in her mothers hands.

"This is a very special locket, sweetie. It's been passed down through several generations of women in our family. Someday, it'll be your locket, too."

"Woah." The teenage girl looked greedily at the beautiful treasure. "When do I get it?"

"When you're mature enough to take proper care of it." She answered with a smirk, shooting a sideways glance at her daughter.

"Well so-_rry!"_ Myra retorted, throwing her arms up in defeat. "I didn't know I wasn't _mature_ enou- yeek!" She was cut off mid-sentance by a rumbling crash that shattered the dock. The sand crumbled beneath their feet, and the railing cracked and splintered under their hands.

"Oh!" The older woman wailed as a particularly nasty lurch ripped the locket form her hands and plunged it into the icy deep water.

...

"_Damn_ Guy, you're some kinda robot!" The jovial pre-teen laughed and flipped his wet, clumpy dark hair out of his eyes.

"How... *Gasp*... long?" An 11-year-old Guybrush Threepwood sputtered as he broke the surface of the water.

"I forgot to count. Really, really, inhumanely long?"

Guybrush sighed dramatically. "I'm trying to achieve something here, Skylar! How can I know if I made it five minutes if you can't keep count?"

"It was way longer than five minutes, man. How do you do that?"

"I dunno. I just can. You really think I beat five minutes?"

"I think you should go for ten!" Skylar said, his eyes suddenly wide. "Do you realize how useful that could be? To be able to stay underwater for ten minutes?"

"Yeah..." Guybrush's eyes widened to match his friends, and they sparkled with excitement.

"Guybrush!" A voice from further down the dock drifted over. "Hey, are you down here?"

"Whaddya want?" The young blonde shouted back, agitated at his sister's interruption.

Myra jogged over to him. "Just a warning: Stay away from mom. She's really steamed."

"What'd you do?" Skylar shot her a mock suspicious glance.

"Shut up." Then, to her younger brother: "She dopped some really old family heirloom into the water when the dock shook just now. Further down the beach, where the water's really deep. So, y'know, just leave her alone for a bit." She stalked off, leaving the boys alone again.

Even before Myra finished talking, Skylar was already putting two and two together in his head.

"Hey Guy, I have an idea," he stated as the pair watched the older girl walk down the shore. "Maybe you could go get that family thing, whatever it is."

Guybrush turned to him. "In the deep area? Are you nuts? It goes on forever. I don't even know if it has a bottom."

"Well, you're probably the only person on the island who could find out."

Guybrush, never one to think things through, changed his mind rather quickly. "Well, all right. It's worth a shot."

The two boys quickly discovered, however, that it was not going to be so easy. First, they had to find the exact spot Ruth had been standing when she dropped it. After some careful footprint studying, they believed they had it pinpointed. There were also other issues they hadn't counted on, like the strong currents. Any time Guybrush dove, he ended up going more sideways than down. He attempted to solve that by climbing down the rocky side of the shoreline, but that slowed him down so much that he didn't get much deeper than when he was being yanked out to sea.

Skyler was out of ideas, but Guybrush, who even at a young age had a knack for puzzle-solving, came up with one last plan.

"What if we found something really heavy, like a big rock or an old anchor, and I just grabbed onto that and let it carry me to the bottom. If it started to feel like I was going too far down, I could just let go and float back up. And that would get me down there really fast, so I could go further using less air, _and_ it would be strong enough to resist the currents."

"Okay let's do it. I'll help you find something to sink with."

The two scoured the beach for awhile and eventually found an ancient, abandoned cannon that they managed to drag back to the edge of the shoreline.

"Okay, I'm gonna hold on tight to the cannon, then you push it into the water." Guybrush instructed.

"Okay. You ready?" Skyler asked, after his friend had wrapped his arms tightly around the nozzle and taken a few deep practice-breaths.

Guybrush nodded, looking suddenly nervous as the thought of a million things that could go wrong flooded his brain.

"I'll stand watch. If you don't come back up after five minutes, I'll go for help."

Guybrush smiled weakly. "Don't forget to count this time."

"No promises." And he gave the canon a mighty shove and sent it hurtling down towards the water.

The more time passed, the more nervous Skyler became. At two minutes, his heart started to beat faster. At three, he started to feel sick to his stomach. By four he was panicking, and paranoia was making him doubt himself. _What if I was wrong before? What if it was less than five minutes? What if he's drowning already?_

By the time it was four minutes and thirty seconds, Skylar was planning out how to tell Ruth he'd killed her son.

At four minutes and forty-five seconds, he realized he had to do something.

At four minutes and fifty seconds, he dove into the water.

The water was surprisingly clear, but even with full visibility Skyler couldn't see anything that even vaguely resembled an end to the bottom. It simply kept going until it vanished.

He began frantically swimming downwards, but since he didn't possess the freakish ability to hold his breath longer than anyone else, he soon had to turn back and surface for air. He swam to the edge and grabbed onto a rock, then proceeded to hyperventilate.

"Ohmygodohmygod what have I done?" Skylar panicked. Suddenly, he realized that he'd stopped counting. He forced himself to calm down. The last time he'd remembered clocking was five minutes. He knew he could hold his breath for about two minutes. _So that makes it what... seven?_

Seven minutes. No way.

The dark-haired boy glanced down at the water again, hopelessly. _I should've known he'd be too determined to let go of that cannon if he needed to. Now he's probably dying down there somewhere._

Just as he was about to give up all hope, though, he saw a glimmer of white against the endless darkness of the deep ocean.

_Guy's white shirt?_

Skyler took another deep breath, which was exceptionally difficult since he'd started to cry, and dove down towards the glimmer.

...

Guybrush tightened his grip on the cannon as it sank lower and lower into the endless depth. In less than ten seconds he surpassed the deepest point he'd made in his previous attempts, and there was still no sign of the ocean ending anywhere. After thirty seconds of falling, he began to worry that he wouldn't make it, but his determination to succeed overpowered the fear, and he dutifully hung on as the plunge continued. After a few more seconds, the boy's head strted to ache and his ears felt like they were going to explode. He was pretty sure his eyes were watering, but it was hard to tell underwater. At one point he was almost positive he was upside-down for a few seconds.

_How much further...? _ He wondered hopelessly.

On a whim, he looked down, and to his surprise, saw the ocean floor rapidly approaching.

_I made it!_ He thought excitedly. For though he'd been determined to succeed, the fact that it suddenly seemed possible gave him a rush of adrenaline.

The cannon hit the floor in a swirling rush of sand and seaweed, and for several precious seconds, Guybrush had to remain still because he couldn't see. As the sand cleared, he began his search for the mysterious heirloom.

It was at that moment that he realized he didn't know what it was.

_Well,_ he reasoned, _I'll know it when I see it._ Guybrush held on to pieces of rock and various seafloor plants to keep himself from floating back to the surface as he dug around.

After a few minutes of searching, the scrawny boy realized that he was running out of breath.

_Damn! And I still have to get all the way back to the top!_

He began to look more frantically, when a flash of gold caught his eye. He scooped up the object and examined it.

_Some kind of locket. Is this it?_ He decided to hope that it was, and began to swim towards the surface as fast as he could. Luckily for Guybrush, humans float, so it was a quick trip. However, he was already lightheaded from the rapid pressure change, and running out of air only intensified his headache. Black spots began to dance in front of his vision, and soon he could barely focus on moving upwards.

_I hope the current doesn't take me too far away..._ Was his last coherent thought before he drifted off.

...

When Guybrush awoke, he was on the beach, with three concerned-looking faces looming over him. One he recognized as Skylar, but the other two took him a longer time to register. They were both women, and both a little past middle-aged. After a few seconds, when his brain started working again, he remembered that they were Chloris and Elizabeth, two of his mom's friends, and also two of the island's resident nurses. After a few more seconds, he realized all three were talking at him. He was about to respond, when he suddenly remembered the most important thing: the locket. He began searching his pants and vest pockets.

"What's wrong dear?" Chloris was saying as she touched his arm gently.

"Locket! The locket." He mumbled. He leapt off the ground and began sifting through the sandy floor for it. "Did I drop it...?"

"Is this what you want?" Elizabeth asked, holding up a gold necklace.

"Yes! Yeah, that's it." Guybrush looked relieved.

"You were holding it when I dragged you up out of the water." Skyler told him. "Is that it?"

"I hope so." Guybrush said. "I found it at the bottom."

"the bottem of _what?"_ Elizabeth inquired, raising an eyebrow.

"Uh... the ocean?"

"How'd you get to the bottom of the ocean?" Chloris cut in.

Guybrush and Skyler spent the next couple of minutes recapping their hairbrained scheme to the two women. The further they got into the story, the stupider it sounded to their own ears. By the end, they felt foolish for even attempting it in the first place. The nurses seemed to agree.

"Well," Guybrush offered in conclusion, "it worked, didn't it? I mean, I got the heirloom."

"That doesn't mean it was a good idea. You could have just as easily drowned. And I think you're more important to your poor mother than that necklace." Elizabeth explained wisely.

"Sorry Beth." Skyler and Guybrush apologized humbly.

"You're lucky to be alive." Chloris told him. She turned to Skyler. "How long was he down there before you fished him out?"

"Uh... eleven minutes? Ish?" Skyler offered.

"Uh-_huh._" They clearly didn't believe him.

"It's true!" Guybrush added eagerly. "I made it to almost ten minutes before I passed out! I was counting!"

Chloris and Beth glanced uncomfortably at each other.

"If you say so." Elizabeth finally conceded, halfheartedly.

"Guybrush! Guy, are you there? Is everything okay?" The frantic voice of Ruth cut through the lull in the conversation. She was practically sprinting down the beach to get to her son and the small congregation gathered around him.

"Hi mom! Yeah, yeah I'm fine."

"Oh, what a relief. I heard you'd nearly drowned yourself and i just about -"

"Look! Hey, look! I got it!"

"Huh?" Ruth snapped out of her rant for a moment. "Got what, dear?"

"Your locket. See?" Guybrush pushed the small gold necklace under his mothers nose.

Ruth clearly was at a loss for words. She stammered incoherently for a few seconds before finally just giving Guybrush a bone-crushing hug.

Before Skyler even had time to comment, however, a piercing cry from the town watchman echoed across the Pillage Island that made the whole group realize why the dock had shaken in the first place.

"_PIRATES!"_

**BWAHAHA! I leave you all with a cliffhanger. Well, not really, since I'm sure you can all guess what's coming. That's right, in the next chapter, I hope to delve into why Guybrush wanted so badly to be a pirate the day he washed up on the shores of Melee Island.**


	2. Chapter 2

**Sorry for the delays, I thought I'd have more time to write now that I'm out of school, but my summer's been busy so far and things didn't work out that way. At least I have a chapter for you now! Enjoy!**

**Any and all reviewers get a virtual hug!**

"Guybrush, Skyler, go home right now," Ruth instructed. She feigned calmness, but her voice was shaking. "Hide in the cellar under the kitchen. Go!" She pushed them forward.

The boys ran as fast as they could towards their street, but Guybrush slowed to a stop as soon as they were out of sight of the panicky women.

"Guy, what are you doing? C'mon!" Skyler urged, nodding his head in the general direction of safety.

"I wanna go see the pirates." Guybrush stated, eyeing his friend evenly.

"Why? Couldn't they like... kill us or something?"

"So? We'll just stay hidden. This is probably the most exciting thing that's ever gonna happen to this boring old island, and I want to see it. Besides, I've never met pirates before. Who knows what they're like?"

Skyler's better judgement was clouded by excitement, and he quickly agreed to follow. The two boys doubled back and ran down a quiet alley towards the docks again. As they approached, they took refuge behind a giant boulder near the shore and watched as hordes of loud, swaggering pirates rushed docks, charging the meager defence that the town's men had managed to set up with a few minutes' notice.

"This could be bad." Skyler whispered worriedly. "It looks like those pirates could overtake our whole island."

"Well, maybe we should help then." Guybrush suggested.

"Help?" Skyler turned to look at him in disbelief. "Help how?"

"I dunno; I'll think of something. But we're not going to accomplish anything sitting here."

"Five minutes ago you _wanted_ to sit here!"

"I never think of the past, only the future. Now come on!" The blonde boy grabbed his friend by the arm and dragged him back towards the center of town.

"Okay, now what, hotshot?" Skyler glared at his friend, raising an eyebrow.

"Umm..." Guybrush scanned the now-deserted town square, trying to come up with some kind of plan. He saw a large stack of barrels against a building that they could climb. "Maybe we could go up onto the roof of that shop, and drop stuff on the pirates' heads as they run into town. That building is along the only pathway into the town square, and they're probaly going to want to come here eventually."

"What the hell would we drop?"

Guybrush hadn't thought of that yet. "Something heavy enough to stun them, but light enough that we could carry a bunch of it up there."

"What would that be?"

"How should I know?"

"It was your idea!"

Guybrush stopped listening to the other's complaints and focused in on finding something to pelt the pirates with. Suddenly, he realized how to solve two problems at once. "We cna chuck the barrels leading up to the roof. That's something we have easy access too, and it'll stop anyone from climing up after us!"

Slyler was growing less and less happy by the minute. "Or - here's a new idea - we could just _go home_ like we're supposed to_._"

"But I hate doing what I'm supposed to do!" Guybrush whined. "Besides, this is our chance to be heroes! We'd be remembered for generations as the kids who stopped the pirates! Wouldn't that be special?"

"I don't care about being a hero or about being remembered. I just want to live to see tomorrow."

"Oh, come on, I need your help! You're stronger than me, and I can't lift those barrels by myself."

Skyler sighed. He and Guybrush were usually always together on these kinds of adventures, but he knew his friend had a certain spark that he just lacked. And when it came to something as dangerous as this, he was often the first to back out. But something kept him there this time. Though he was complaining, he didn't really want to leave. He wanted to be a part of this. He wasn't sure why, but he was pretty sure it had something to do with pirates. Since they were little, he and Guybrush had admired pirates, and deep down, they'd been wishing to meet some for years. Maybe this was their chance. And that train of thought led him to a better idea.

"Hey Guy?" He ventured. Guybrush was busy begging him to stay and hadn't noticed Skyler's momentary lapse in thought.

"Pretty _pretty _plea- yeah?"

"What if, instead of attacking the pirates, we like... tried to join them? We've wanted to become adventurers for our whole lives, right? Get off the island, make something of ourselves. This could be our chance. Our _only_ chance."

Guybrush's eyes widened. "Hey, you're right! I never thought of that. Let's go become pirates!"

**Sorry for the short, lousy chapter and the lack of an ending here, but I wanted to get something out since I haven't updated this story in a while. This is probably gonna become a threeshot, so stay tuned for the final chapter, coming eventually!**


	3. Chapter 3

**The final chapter! I'm quite frankly kind of glad to be done with this story. It's certainly not my favorite thing I've ever written, but meh. Enjoy!**

"But wait... how do we become pirates?" Guybrush inquired, looking at Skyler expectantly.

"Ask them?" He suggested with a shrug. "I'm not sure. I don't know what pirates are like. Do you think they'd let us?"

"Asking seems like a good enough plan." The naive Guybrush agreed with a nod. "C'mon then, let's go find some pirates!"

The boys took off, cutting through a small cobblestoned streed crammed with various shops and taverns. Halfway accross, however, they heard voices and footsteps running towards them, growing louder by the second.

Skyler's first instinct was to hide, and that's just what he did. He leapt behind the wall of the nearest building. Guybrush, however, who was apparently born without basic survival , instincts, waited out in the open with minimal caution.

When the approaching sounds grew to a dull roar, Skyler began to panic. He suddenly wanted nothing to do with pirates at all. He wanted to go home, crawl into bed, and wait for it to be over. But Guybrush was never going to go for that, he knew.

Suddenly, a crowd of disgruntled pirates appeared at the end of the street, charging towards the hidden Skyler and the very much in plain sight Guybrush.

"Hey! Excuse me!" Guybrush called, waving his arms. Skyler nearly facepalmed.

The pirates, however, apparently had more important things to do than listen to a couple of kids, and most ofthem charged by without so much as a second glance in the blonde boy's direction. One, however, slowed down and looked at him.

"Whadda you want, kid?" He asked gruffly.

Guybrush drew himself up to his full height, looked the pirate in the eyes and stated, "I'm Guybrush Threepwood, and I wanna be a pirate."

The pirate laughed, a loud, booming sound that made Guybrush's heart vibrate in his chest.

"Go home, Driftwood." The pirate turned to leave, but only made it a couple steps before Guybrush reached out to stop him. Before he could say anything, however, the pirate wheeled around and struck him across the face.

"Get _lost_." His voice was low and menacing.

Guybrush looked as if he were about to protest again, and Skyler saw from his position the pirate reach for his belt, where he no doubt had some kind of deadly weapon. Before he knew what he was doing, he'd picked up a tree branch from the ground next to his feet and leapt from his hiding place with a noice that had been intended as a threatening growl but came out more as a yelp. The pirate turned slowly to face Skyler, but before he had the chance, he'd swung the branch. It collided with the burly man's face with a dull thud and he stumbled backwards.

Guybrush took the moment to drop to the ground and grab the pirate's ankle, sending him to the ground with a thundering crash. The collosal man was stunned and couldn't move for a moment. Skyler just stared at him, but Guybrush's voice shook him from his trance.

"Hey! Come on, let's get out of here before he gets up!" Guy urged, grabbing his friend's arm and dragging him away. Before they'd made it even a few steps, however, the pirate was back on his feet and charging towards them.

"Split up!" Guybrush suggested, and the two took off in opposite directions. Skyler dove towards a building, hoping to get inside, and Guybrush started hastily scaling the wall of a tavern to reach safety on the roof.

After a moment's hesitation, the brute went after Skyler, who had unfortunatley chosen a shop he couldn't get into and was trapped against the door.

Guybrush jumped down from the wall and ran towards his helpless friend as quickly as he could. The pirate heard him coming and whipped around. Before Guybrush could react, the man slammed the blunt end of a sword into his head. He was out before he even fell over.

When Guybrush awoke, the pirates were gone. So was Skyler.

...

"Elaine! Will this island do?" Guybrush called to his very annoyed wife.

"Yes, dear, any land will do. Just somewhere we can make repairs." She answered, trying to reign in her anger. It wasn't her husband's fault that their helmsman had run them into a rock and effectively taken out half the ship.

Soon enough, the ship had been docked and the Elaine had set each crewmember to work with some task usefull to fixing their ship. All of them except Guybrush.

"What can I do to help, dear?" He asked as sweetly as possible.

"You can stay out of the way, Guybrush. Go entertain yourself at a tavern or something."

"Yes dear." He said brightly.

Guybrush strolled along the island until he reached what appeared to be a very popular bar, judging by the din coming from inside. He cautiously pushed open the door.

The room bar was indeed popular. It was full of people from wall to wall, drinking grog, playing darts, and talking. Guybrush made his way over to the bar. The bartender was talking to some patrons on the other side of the tavern, laughing loudly. Guybrush guessed he was probably drunk.

The man sitting next to Guybrush turned to face him. "Don't worry about that bartender, he's just -" Abruptly, he stopped.

Guybrush, who had been looking at the grog barrels on the wall up until that point, turned to look at the man who was addressing him.

"Long time, no see."


End file.
